Jean Quan Versus the World

Ellen Cushing | May 28, 2014 | Story Politics

Editor's Note: This is one of many dispatches from Oakland that San Francisco is publishing over the next month, all part of our June "Oakland Issue." To see the rest of the issue's contents, and to read stories as they become available online, click here.

Jean Quan is exhausted. It’s 7 p.m. on a Thursday in late March, and the mayor has been working since 5 a.m., when she started her morning, as usual, by reading the Oakland Police Department’s daily briefing. The dinner we’re eating—spring rolls and curry salmon at an otherwise empty Vietnamese hole-in-the-wall across Frank H. Ogawa Plaza from City Hall—is her first real meal of the day. Sitting at a glass-topped table, Quan has the bleary-eyed look and monosyllabic affect of someone who has had a very, very long day—or series of days, as the case may be.

In recent months, Quan has been buffeted by one piece of bad news after another. The city has had three city administrators since March and four police chiefs since the fall of 2011; Quan’s most recent city administrator appointment, Fred Blackwell, jumped ship after just a month on the job. Last fall, the Domain Awareness Center, a proposed intelligence-gathering hub that Quan supported, stirred outrage among civil libertarians in the city. In April, she made the mistake of asserting that the crown prince of Dubai had partnered with the city on a sports stadium development, a claim that she was almost immediately forced to retract. A few days later, the Golden State Warriors officially announced their long-discussed decision to abandon Oracle Arena in favor of a waterfront stadium across the bay. That same month, the A’s rejected the city’s offer of a new 10-year-lease on the Coliseum.

And then there’s Oakland’s biggest problem: crime. Despite some small signs of hope—homicides, for example, were down in 2013 from the previous year—and a seemingly endless list of proposed solutions, the city’s sky-high violent crime rate isn’t significantly or consistently lower than it was a decade ago, and its police department is still desperately understaffed (it has 652 officers, at least 200 fewer than it should by most accounts). Over the last five years, the city has suffered an average of 104.2 homicides a year (by comparison, San Francisco, which has more than twice the population, had 48 murders in 2013). Last year, it earned the unwanted honor of being named the robbery capital of the United States. As Greg McConnell, a consultant and the president and CEO of the Oakland business group Jobs and Housing Coalition, puts it, “Crime is more than a perception. It’s a reality.”

Of course, it isn’t fair to blame Quan for all of this. But politics isn’t fair—and Quan has brought a lot of her woes on herself. Although her progressive bona fides rank with those of any mayor in the country, she has managed to alienate the far left and middle-of-the-road moderates alike (there are no conservatives to speak of in Oakland), a dubious achievement that was primarily a product of her erratic response to the Occupy movement. Oakland’s sizable radical wing has denounced Quan for abandoning her activist roots after becoming mayor, while the business community and the affluent hills constituency have accused her of being soft on crime and hard on business. In three and a half years, the mayor has been the subject of no fewer than three recall campaigns—and observers suggest that those efforts failed not because there wasn’t enough Quan animus out there, but because her foes couldn’t get their acts together to organize petition gathering. As of March, her approval rating was an abysmal 24 percent.

But Quan is nothing if not a relentless optimist, a side of herself in full view at tonight’s dinner. She talks about new business coming to the city; about plans for Brooklyn Basin, a 3,100-unit, $1.5 billion development along the waterfront whose funding she helped broker; about the New York Times having named Oakland the fifth-best place to visit in 2013 (a plaudit she repeats so often that it has become something of a joke in the city’s political circles). “We’re making real progress,” she concludes. “And to make change we need to have some continuity. That’s why I’m running.”

Suffice it to say, winning won’t be easy.

Not surprisingly, Quan’s five major competitors are all basically running on variations of “I’m not Quan,” with differing topspins. Civil rights lawyer Dan Siegel is touting his progressive credentials. City auditor Courtney Ruby is selling herself as a no-bull straight talker who’s unafraid to weed out corruption and waste. Joe Tuman, a San Francisco State political communications professor and former TV political commentator, is promising to focus on the city’s public safety crisis. Libby Schaaf, who currently occupies the city council seat that Quan vacated, is portraying herself as a good-government candidate and an experienced, effective leader with consensus-building skills. And businessman Bryan Parker has come from nowhere to amass a large war chest and a fair amount of name recognition by crowdfunding his campaign.

In fact, many of her challengers’ positions are not demonstrably different from Quan’s. Because of this— and because the field may not be completely settled, with anxious rumors still floating about possible runs by city council member-at-large Rebecca Kaplan, Congresswoman Barbara Lee, and former city councilmember Ignacio De La Fuente—it’s too early to handicap the race with any accuracy. Kaplan, who enjoys strong popularity throughout the city and finished third in the 2010 mayoral sweepstakes, has not yet endorsed anyone. Nor have any of the other sitting Oakland councilmembers or any of the city’s churches, which retain sway among Oakland’s robust African-American middle class. While Quan earned support among many of the city’s politically powerful unions back in 2010 and easily could again, nothing is guaranteed.

Then there’s the murky element of ranked-choice voting, which allows voters to select first, second, and third choices, thus benefiting nonpolarizing, inoffensive candidates who garner broad support. In an election with a multitude of viable candidates, a last-minute cash infusion or a big-name endorsement could tip the scales. But the voting system also means that Quan’s rivals could easily knock each other out. “Ranked-choice voting throws everything into upheaval,” a close observer of Oakland politics recently told me, “and you don’t have any strong elders with major name recognition who can replace Jean Quan.” Historically speaking, it’s difficult to unseat an incumbent, even one as unpopular as Quan—a May Jobs and Housing Coalition poll (which included De La Fuente) placed her above all the other candidates, even though her share of the vote was a middling 20 percent. But if there were ever a place or a time or a constituency to make that happen, it might be Oakland in 2014. It all depends on which of the candidates breaks through the noise.

People call Libby Schaaf the ”Girl Scout barracuda.” At least she says that people call her that. In any case, it’s apt—Schaaf is one part obedient politeness and one part steely-eyed ambition. When talking to her, you get the distinct sense that she was very popular in high school. (As it happens, she was a cheerleader for the Skyline High Titans.) Politically, too, she’s a bit of a rule follower, at least insofar as she’s come up through the ranks deliberately—as chief of staff to then–council president De La Fuente, then as a special assistant to then-governor Brown, then as a councilmember herself. “Almost every single job I’ve had has been around trying to make this city better,” Schaaf says. “I have a lifetime of relationships here.”

Schaaf is a moderate—or at least a moderate by Oakland’s standards—who has managed to appeal to progressives as well by siding with the city council’s lefty wing on several important issues, like youth curfews. She’s a proponent of community policing, but, unlike some of the race’s more radical candidates, she’s also in favor of increasing the size of the city’s police force. She’s made a mission out of government transparency and tech innovation—Code for America’s Jennifer Pahlka was an early supporter—but she hasn’t staked her entire candidacy on them.

Schaaf has few skeletons in her closet and strong approval in her district as well as among many of the city’s tech-savvy young progressives. Further, as a sitting city councilmember, she has the kind of face and name recognition that only Quan can match. (Indeed, over an hour-long coffee interview at a busy downtown Oakland cafĂ©, Schaaf sees no fewer than four people she knows, waving and smiling at them without skipping a beat as she discusses her platform with me.) And, perhaps most tellingly, she’s hired as a consultant Ace Smith, a 30-year veteran of Democratic politics who managed Antonio Villaraigosa’s winning bid for L.A. mayor in 2005 and was part of the team that catapulted San Francisco mayor Ed Lee to victory in 2011.

Long before she officially announced, Schaaf was floated as a clear threat to Quan, and in a less crowded race she could be a shoo-in. (The May poll from the Jobs and Housing Coalition ranked Schaaf in second place, with 15 percent.) But the logic of ranked-choice voting can be a mystery even to its closest observers, and if Schaaf chooses not to enter into an “Anybody but Quan” ticket, she could easily split the vote with a like-minded candidate.

That candidate may well be law-and-order moderate Tuman. Balding, trim, and boundlessly energetic (he runs Ironman triathlons), Tuman was born to be in front of a TV camera or behind a podium. In 2010, he ran a well-respected but ultimately unsuccessful campaign for mayor, finishing fourth but earning a not-insignificant portion of the vote and a fair amount of name recognition.

This year, he appears hell-bent on winning. And because he entered the race relatively early, in July, he’s had nearly a year to hold house parties and court voters. As of the January 31 reporting deadline, he’d raised $145,350, the second-largest amount of all the candidates (including Quan), though Schaaf didn’t enter until December and was coming up fast less than two months later. Tuman asserts that he will have “pretty much a singular focus” on crime, but his policy proposals aren’t that different from the rest of the field’s. He opposes stop-and-frisk measures by the police, says that there’s no chance that antigang injunctions and youth curfews will be approved, and wants to raise the force to 900. (Quan says 800; Schaaf says “at least” 800 and ideally 925; Siegel, on the far left, wants to add just 48 cops to the existing 652.)

“I’m going to have a limited bandwidth here,” Tuman says over coffee on a warm March afternoon, using one of the corporate turns of phrase to which he’s noticeably prone. “And I have some objectives and outcomes that I want to manage towards.” He’s fond of drawing a comparison between himself and ex-mayor Jerry Brown, who famously (and mostly successfully) set out to bring 10,000 new residents to downtown Oakland as part of his 10K plan. “If you have an executive who’s gonna put most of their energies into a singular objective,” Tuman says, “they’re gonna be more effective at managing that outcome.’’

In a city like Oakland, doubling down on crime will likely appeal to a broad swath of voters, especially among Tuman’s base in the wealthy hills. According to McConnell, every poll of Oaklanders that the Jobs and Housing Coalition has conducted since 2005 has indicated that public safety is a primary concern for a majority of Oaklanders; in the most recent such poll, in fact, three-quarters of respondents listed either crime and public safety or gangs and youth violence as the most important issue facing the city. But crime is a much bigger and more unpredictable beast than urban development, and Oakland’s crime rate has stayed more or less the same for four decades. Tuman isn’t just throwing all his eggs into a single basket—he may be using a basket that has a hole in the bottom.

“It’s clear that crime is at the top of Oakland’s mind,” says McConnell. “But the difficulty that any mayoral candidate will have with making crime their only issue is, what the hell are you going to do about it? After you win, you have to govern. And this is a hard city to govern.”

Still, Tuman is adamant: “Voters are looking for someone who can accomplish some specific objectives as opposed to making a whole bunch of promises that may or may not come true.” He sips his coffee, staring me in the eye.

“This message has traction. I can win this race.”

Both Tuman and Schaaf are coy about their critiques of the mayor, preferring so far to emphasize a positive message. Courtney Ruby is not so restrained. In her role as city auditor, Ruby has presented herself as a city watchdog, and as a candidate, she’s played up her history of, as she says, “holding Oakland’s leadership accountable.”

“Citizens know the city’s not working,” she says. “All you have to do is drive down the street and feel the city crumbling under your car. I’m going to make decisions based on the truth—telling it like it is. I am not about lip service. I am about accessibility.” Ruby is a forceful speaker with a compelling story—a single mother of two adopted sons. But she is likely to become the victim of a crowded race and an opaque voting system. And running on a platform of weeding out waste and corruption in a city that’s not necessarily known as a hotbed of either is risky: As McConnell says, “Chicago has corruption. Oakland has incompetence. In our polling, corruption ranks in the single digits in terms of voter concern. Courtney says she’s running to clean up Oakland government. But I don’t know if mayor is the best position to do that. Auditor is.”

Or, as another close observer of Oakland politics told me, “I can’t wrap my head around why she’s running now.” Ruby lacks the name recognition of Quan, Schaaf, and Tuman and the niche appeal of Bryan Parker and Dan Siegel. She’s a well-spoken mother of two in a race that already has one in the form of Schaaf, and a tough-talking transparency advocate in a field full of them. With the most recent poll giving her 4 percent of first-choice votes, it’s unlikely that she’ll win, but she has a solid shot in 2018, or 2022, or 2026. After all, citizens will likely feel that the city’s not working then, too.

The most significant moment in Dan Siegel’s mayoral campaign came long before he declared, long before he’d even really thought about running. It was in the frenzied days of fall 2011, after Occupy propelled the city onto the front page of the New York Times and into thrumming collective anxiety. That was when Siegel—a civil rights lawyer and former school board member—very publicly left his post as an unpaid legal adviser to Quan, a longtime friend dating back to their days at UC Berkeley, over what he told the Chronicle at the time was a “tragically unnecessary” use of force at Occupy.

The story had just enough gossipy salaciousness to make headlines, and since then, Siegel has continued to establish his progressive bona fides. In the first debate, on the trail, and in person, Siegel has advocated almost doubling the city’s minimum wage, to $15 (it’s currently $8, the state minimum), and establishing community gardens throughout the city. He’s come out strongly against the Domain Awareness Center as well as the various tough-on-crime measures that are floated in Oakland every few years: youth curfews, antigang injunctions, stop-and-frisk. He takes descriptors like “radical” as a compliment and is fond of saying that Oakland “can’t jail and arrest its way to public safety.”

“Oakland has a huge amount of promise,” he tells me in the downtown Oakland offices of the civil rights law firm he has run for decades, Siegel & Yee. “And it deserves much better political leadership. I’m looking at what’s happening across the country—whether it’s New York or Seattle or Jackson, Mississippi—and seeing people opting for a more progressive, democratic, egalitarian option in politics. And I think we can do that in Oakland.”

That implicit comparison to New York and Bill de Blasio may sound grandiose, but it’s not necessarily all that far off. Both de Blasio and Siegel are longtime, well-respected, highly principled progressives who compellingly and unabashedly positioned themselves to the left of the field in crowded races in very left-leaning cities. Both worked to cobble together a base of dyed-in-the-wool lefties, young radicals, and people of color—groups that are both large and frustrated in Oakland. Save for the first, however, they don’t always vote, and getting his fan base to the polls might be Siegel’s biggest challenge. But maybe that’s not the point: Though Siegel claims that he’s in the race to win it, he also seems perfectly happy to act as a Nader-esque progressive foil. (He’s currently polling at 5 percent.)

Siegel’s candidacy will most likely pull more votes from the staunchly progressive Quan than from the other contenders. If a solid chunk of Oakland’s left wing votes for him over her, he will have gotten her out of office and, he hopes, moved the debate to the left. (In fact, defeating Quan will likely result in a less progressive candidate winning—again, the Nader effect.) “You have a city here with problems that result from poverty and unemployment and homelessness and hopelessness,” he tells me. “And you have candidates who are not really challenging anything about the status quo. I think the whole thing needs to be turned upside down.”

During the months that I have spent talking about this race with fellow Oaklanders, the same refrain has repeatedly come up: What’s the deal with Bryan Parker?

It’s a good question. Parker, a member of the port commission, entered the mayor’s race auspiciously: In June, he promised to join the fray if he could raise $20,000 in 10 days using the crowdfunding website Crowdtilt. He surpassed that goal in less than 24 hours, ultimately raising nearly $60,000, making him the most well-funded candidate on the ticket as of the December 31 filing deadline—and ensuring that a voting public that had never heard of him before suddenly knew his name. (Indeed, Parker’s name recognition is climbing fast, according to the May Jobs and Housing Coalition poll, and he’s polling at a relatively respectable 7 percent.)

In person, Parker is a bit like the human equivalent of the campaign: undoubtedly charismatic, somewhat fascinating—and completely perplexing. He’s the only major African-American candidate in the contest, but he’s not tailoring his message to the black community. A vice president at a healthcare company before entering the race, Parker has little experience as a public official (save for his time on the port commission, to which he was appointed) and next to no campaign experience. His speech is quick, tangent-riddled, and eager in the manner of a college kid trying to impress a professor. In about four minutes of conversation, he happily zigzags from a discussion of the work of Cornel West, to the thinking of the Enlightenment, to his childhood in Stockton, to the digital cryptocurrency Bitcoin (which he hopes to “incorporate into city government”). He occasionally talks about himself in the third person and has at different times expressed nearly mutually exclusive political positions (for example, in our interview, he spoke about police brutality; a mere two weeks later, he said on record the city has “too many people watching our officers”).

But money talks, and Parker has already launched an aggressive online ad campaign and blanketed the city with signs. “Bryan Parker is in play,” says McConnell, especially within the city’s business and tech circles. His experience in the private sector is a selling point for some members of the business community, and his position as a bit of a technocrat appeals to people who want to see Oakland get a piece of San Francisco’s tech-fueled mega-growth. If he is smart about courting the African-American middle class, he could make a strong enough finish to get his name out there for a mayoral or city council election down the line.

Back at the Vietnamese-food place with Quan, we talk about the OPD and Occupy and Deanna Santana (who has just left her post as city administrator). But the most interesting part of our conversation comes about half an hour in, when I ask Quan what her weaknesses are. It’s a pat, routine question, the kind that most politicians—especially those used to being on the defensive, as Quan is—are surely familiar with. But she pauses so long that I begin to think she didn’t hear me. “Let me put it this way,” she finally says. “If I had to do it again on different issues, I’d spend more time building consensus.” Another 40...45...50 seconds of silence pass. “I get into this real Asian-American thing of thinking that working hard is good enough. And it’s not. I tend not to communicate about what I’m doing, and I tend not to ask for help. I’ve had to think a lot about that, and learning how to trust other people and ask for help. A good politician does that. I’m not always a good politician.”

All of which might sound like classic false modesty coming from the mouth of a career politician but for this fact: It is completely true. In a little more than three years, Quan has shown herself to be a competent public servant and a lackluster leader. She’s given to quiet triumphs and loud gaffes, largely due to her wobbly communication skills and an unfortunate habit of fudging numbers and facts rather than admitting that she doesn’t know them (see the recent prince of Dubai snafu). She is malapropism-prone and criticism-averse and almost willfully uncharismatic. She gives terrible hugs.

All told, she is the rare elected official who manages, simultaneously, to be nearly universally praised for her work ethic and nearly universally criticized for her actual work. Amid the vitriol and the recalls and the polling numbers, it’s easy to forget that since 2011, Quan has delivered two balanced budgets, attracted major investment, and wrestled significant concessions from the city’s most powerful union, the Oakland Police Officers’ Association.

It’s also easy to forget that Quan has never lost an election. Four years ago, when she leapfrogged over the well-connected and moneyed former state senator Don Perata in the city’s first ranked-choice election, her candidacy became an overnight object lesson in the smart way to beat the new system: Campaign tirelessly, make few enemies, ally yourself with other dark horses, and earn enough second-place votes to eke out a victory. But this year, the very thing that catapulted Quan to city hall—the system’s preference for inoffensive, non-polarizing candidates who can convince enough people to vote for them in the second- or third-place slots—could easily be her downfall. As of the May poll, she had an unfavorable rating of 54 percent, and even though 20 percent of those polled would vote for her in their first-choice slot, only 7 percent said they would vote for her as their second choice.

In other words, Quan is now the Perata of 2014: a divisive figure who has some fans, especially in her East Oakland home district and among Asian-Americans, but also faces plenty of people who would rather vote for anyone else. In 2010, Quan was the de facto leader of the informal “Anybody but Don” coalition. Now, just four years later, a successful “Anybody but Quan” tactic doesn’t seem all that far off.

In spite of that, or maybe just because it’s the right thing to say, Quan, tired but unflagged, again and again expresses her characteristic confidence. “Yes,” she says when I ask her if she thinks she’ll win. “I think it’ll be tough. But I’m gonna win.” This time, she doesn’t pause at all.

Originally published in the June issue of San Francisco.

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